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Methyl 3-(trimethylsilyl)propiolate

  • CAS No. 42201-71-8

  • Cat. No. CS-0128831
  • Purity≥96%
  • MDL No.MFCD04039783

*For research and further manufacturing use only, not for direct human use.

Methyl 3-(trimethylsilyl)propiolate|CS-0128831

Structure of 42201-71-8

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General Information

  • CAS No. 42201-71-8
  • Cat. No. CS-0128831
  • Purity ≥96%
  • MDL No. MFCD04039783
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₂O₂Si
  • Molecular Weight 156.25
  • Synonym(s) Methyl 3-trimethylsilylpropynoate
  • SMILES O=C(OC)C#C[Si](C)(C)C

Description

Methyl 3-(trimethylsilyl)propiolate is a bench-stable, moisture-tolerant alkyne reagent featuring a terminal alkyne functionalized with a trimethylsilyl-protected propiolate ester. This combination enables direct incorporation into Sonogashira couplings and other transition-metal-catalyzed transformations without pre-deprotection. The silyl group stabilizes the acidic alkyne proton while allowing selective desilylation under mild conditions. The methyl ester moiety facilitates downstream derivatization via hydrolysis or nucleophilic substitution. This reagent streamlines access to functionalized alkynes in synthetic and materials chemistry workflows.

Application

Methyl 3-(trimethylsilyl)propiolate serves as a stable, bench-ready building block for alkyne-based transformations. Its terminal alkyne functionality enables efficient Sonogashira coupling and click chemistry protocols, while the trimethylsilyl group provides protection and enhanced solubility. The methyl ester facilitates downstream derivatization, and the molecule exhibits excellent functional group tolerance and ease of purification in standard synthetic workflows.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   1.0402
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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